GB1444684A - Unsaturated phosphonate esters and insecticidal compositions containing such esters or other unsaturated phosphonate esters having synergist properties - Google Patents
Unsaturated phosphonate esters and insecticidal compositions containing such esters or other unsaturated phosphonate esters having synergist propertiesInfo
- Publication number
- GB1444684A GB1444684A GB463174A GB463174A GB1444684A GB 1444684 A GB1444684 A GB 1444684A GB 463174 A GB463174 A GB 463174A GB 463174 A GB463174 A GB 463174A GB 1444684 A GB1444684 A GB 1444684A
- Authority
- GB
- United Kingdom
- Prior art keywords
- reacting
- propargyl
- esters
- diethyl
- dichloride
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 title abstract 4
- 150000002148 esters Chemical class 0.000 title 1
- 230000000749 insecticidal effect Effects 0.000 title 1
- 239000000203 mixture Substances 0.000 title 1
- -1 Unsaturated phosphonate diesters Chemical class 0.000 abstract 6
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 abstract 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract 3
- 239000002904 solvent Substances 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 abstract 2
- TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical compound OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 abstract 2
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 abstract 1
- VMKOFRJSULQZRM-UHFFFAOYSA-N 1-bromooctane Chemical compound CCCCCCCCBr VMKOFRJSULQZRM-UHFFFAOYSA-N 0.000 abstract 1
- YITVQRWHXAYYIX-UHFFFAOYSA-N 1-dichlorophosphorylbutane Chemical compound CCCCP(Cl)(Cl)=O YITVQRWHXAYYIX-UHFFFAOYSA-N 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract 1
- 150000001350 alkyl halides Chemical class 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- LXCYSACZTOKNNS-UHFFFAOYSA-N diethoxy(oxo)phosphanium Chemical compound CCO[P+](=O)OCC LXCYSACZTOKNNS-UHFFFAOYSA-N 0.000 abstract 1
- 239000002917 insecticide Substances 0.000 abstract 1
- 238000010992 reflux Methods 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- 239000011734 sodium Substances 0.000 abstract 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds
- A01N57/20—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds containing acyclic or cycloaliphatic radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4071—Esters thereof the ester moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4078—Esters with unsaturated acyclic alcohols
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Molecular Biology (AREA)
- Agronomy & Crop Science (AREA)
- Biochemistry (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
1444684 Unsaturated phosphonate diesters S C JOHNSON & SON Inc 31 Jan 1974 [9 Feb 1973] 4631/74 Heading C2P [Also in Division A5] Phosphonate diesters of the Formula (I) wherein R 1 is an alkyl or alkenyl radical having 2-12 carbon atoms or is cyclohexyl and R 2 is propargyl, C 1 -C 5 alkyl or 2-(2-butoxyethoxy)- ethyl, with the proviso that R 2 is propargyl when R 1 is cyclohexyl, are obtained (a) (when R 2 is propargyl) by reacting a dichloride R 1 P(O)Cl 2 (1 mole) with 2 mols. of propargyl alcohol in the presence of 2 equivalents of a base, e.g. triethylamine and suitably in the presence of a solvent, e.g. diethyl ether, or (b) (when R 2 is other than propargyl) by reacting the dichloride with one equivalent of alcohol (R 2 OH) and one equivalent of a base and suitably in a solvent and then reacting with one equivalent of propargyl alcohol and of the base. The products are useful as synergists for insecticides and the invention also includes as novel products the phosphonates of Formula I with the added proviso other than those in which R 1 is a C 2 -C 12 alkenyl radical. n-Butylphosphonic dichloride is obtained by reacting diethyl n-butyl phosphonate with PCl 5 at 105 C. for 6 hours. Diethyl n-butyl phosphonate is obtained by reacting n-butyl bromide with triethylphosphite under reflux conditions. Dialkylalkylphosphonates can also be obtained by reacting a dialkyl phosphite, e.g. diethyl phosphite, with sodium in a dry solvent, and then reacting with an alkyl halide, e.g. n-octyl bromide.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US00331165A US3856896A (en) | 1973-02-09 | 1973-02-09 | Alkyl propargyl phosphonates |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1444684A true GB1444684A (en) | 1976-08-04 |
Family
ID=23292874
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB463174A Expired GB1444684A (en) | 1973-02-09 | 1974-01-31 | Unsaturated phosphonate esters and insecticidal compositions containing such esters or other unsaturated phosphonate esters having synergist properties |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3856896A (en) |
| JP (1) | JPS49109540A (en) |
| AU (1) | AU6521574A (en) |
| CA (1) | CA1012548A (en) |
| DE (1) | DE2406783A1 (en) |
| FR (1) | FR2217346B3 (en) |
| GB (1) | GB1444684A (en) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2727479A1 (en) * | 1977-06-18 | 1979-01-04 | Bayer Ag | INSECTICIDES AND ACARICIDES |
| DE2853450A1 (en) * | 1978-12-11 | 1980-06-19 | Basf Ag | THIONOPHOSPHONIC ACID ESTER |
| DE2936037A1 (en) * | 1979-09-06 | 1981-04-09 | Bayer Ag, 5090 Leverkusen | PROPARGYL GROUP-CONTAINING METHANPHOSPHONIC ACID ESTERS AND THEIR USE IN SYNERGISTIC ACTIVE SUBSTANCE COMBINATIONS FOR PEST CONTROL |
| US4428945A (en) | 1980-11-21 | 1984-01-31 | Rhone-Poulenc Agrochimie | O-Alkyl S-(tertiary alkyl) alkylphosphonothioate insecticides and nematocides |
| US4472391A (en) * | 1980-11-21 | 1984-09-18 | Rhone-Poulenc Agrochimie | O-Aryl-s-(tertiary alkyl) alkylphosphonothioate insecticides and nematocides |
| US4472390A (en) * | 1980-12-31 | 1984-09-18 | Rhone-Poulenc Agrochimie | S-Alkyls-(tertiary alkyl) alkylphosphonodithioate insecticides and nematocides |
| GB0211924D0 (en) * | 2002-05-23 | 2002-07-03 | Syngenta Ltd | Composition |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3065125A (en) * | 1960-01-28 | 1962-11-20 | Monsanto Chemicals | Alkynyl phosphonothioates |
| US3071610A (en) * | 1961-07-06 | 1963-01-01 | Dow Chemical Co | O-[1-(chloromethyl)2-propynyl] o, o-dialkyl phosphates and phosphorothioates |
| US3803271A (en) * | 1971-06-01 | 1974-04-09 | Gaf Corp | Organophosphonates |
-
1973
- 1973-02-09 US US00331165A patent/US3856896A/en not_active Expired - Lifetime
-
1974
- 1974-01-30 CA CA191,312A patent/CA1012548A/en not_active Expired
- 1974-01-31 GB GB463174A patent/GB1444684A/en not_active Expired
- 1974-02-05 AU AU65215/74A patent/AU6521574A/en not_active Expired
- 1974-02-08 FR FR7404378A patent/FR2217346B3/fr not_active Expired
- 1974-02-08 DE DE19742406783 patent/DE2406783A1/en active Pending
- 1974-02-09 JP JP49016731A patent/JPS49109540A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| JPS49109540A (en) | 1974-10-18 |
| FR2217346B3 (en) | 1976-11-26 |
| US3856896A (en) | 1974-12-24 |
| CA1012548A (en) | 1977-06-21 |
| DE2406783A1 (en) | 1974-08-15 |
| FR2217346A1 (en) | 1974-09-06 |
| AU6521574A (en) | 1975-08-07 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |